引用本文:
耿欣, 陈才, 李郭成, 高康莉, 邓兆静, 韩国志. 一种冠醚金属卟啉化合物的合成及其阴离子识别机制[J]. 应用化学,
2015, 32(2): 171-176.
doi:
10.11944/j.issn.1000-0518.2015.02.140140
Citation: GENG Xin, CHEN Cai, LI Guocheng, GAO Kangli, DENG Zhaojing, HAN Guozhi. Synthesis of Crown Ether Metal-prophyrin and Its Anion Recognition[J]. Chinese Journal of Applied Chemistry, 2015, 32(2): 171-176. doi: 10.11944/j.issn.1000-0518.2015.02.140140
Citation: GENG Xin, CHEN Cai, LI Guocheng, GAO Kangli, DENG Zhaojing, HAN Guozhi. Synthesis of Crown Ether Metal-prophyrin and Its Anion Recognition[J]. Chinese Journal of Applied Chemistry, 2015, 32(2): 171-176. doi: 10.11944/j.issn.1000-0518.2015.02.140140
一种冠醚金属卟啉化合物的合成及其阴离子识别机制
摘要:
合成了一种冠醚化卟啉化合物(1)及其Hg2+配合物(3),通过紫外光谱研究了冠醚卟啉化合物中卟啉单元与汞离子的配合性能,并采用核磁共振研究了其在溶液中的分子组装机制。利用冠醚环的离子识别行为以及冠醚环与卟啉环的协同作用,研究了冠醚金属卟啉化合物的阴离子识别检测,并对其机制进行了探讨。相比于5-(4-羧基苯基)-10,15,20-三苯基卟啉,冠醚卟啉化合物中的卟啉单元配合汞离子之后,其紫外吸收中的S带由415 nm红移至440 nm处。对于冠醚金属卟啉化合物而言,当其中的冠醚单元配合其特征金属阳离子之后,随着阴离子的不同,其紫外吸收光谱和颜色也呈现不同的特征,为阴离子的可视化识别提供了一种新的思路。
English
Synthesis of Crown Ether Metal-prophyrin and Its Anion Recognition
Abstract:
A benzo-15-crown-5 modified 5-(4-carboxyphenyl)-10,15,20-triphenylporphyrin (1) was synthesized and used for binding with Hg2+ ion to form crown ether metal-prophyrin complex(3). UV-Vis and 1H NMR were used to investigate the formation and self-assembly of complex 3. The difference of 1H NMR spectra of complexes 3 and 2 reveals that a synergy effect of prophyrin and crown ether exists. The anion recognition and mechanism of complex 3 were also studied. After addition of NaNH2,an obvious red shift in the UV-Vis spectra was observed accompanied with a color change from green to chartreuse viewed by naked eye. At the same time,the chemical shift of -CH2- in crown ether ring shifted from 3.12 to 3.16 and 3.32 to 3.34,respectively. This phenomenon can be explained by the strong nucleophilic property of amino anion. However,addition of other sodium salts such as NaCl,NaH2PO4 and NaHCO3 could not result in the same phenomenon. This study provides a method for visible anion recognition.
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Key words:
- crown ether
- / porphyrin
- / synthesis
- / anion
- / visible recognition
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